40 Ways to Celebrate Your Sweetheart on Sweetest Day

Fall is here and that warm and cozy feeling we all get has a way of getting into our hearts and making itself at home there. The third Saturday of October is Sweetest Day, a holiday celebrated mostly in the Midwest, where people shower their significant other with sweet gifts and treats. It’s similar to Valentine’s Day, but more focused on the idea that small tokens of appreciation and inexpensive experiences can make a loved one’s life all the more sweet. While there are plenty of ways to surprise your significant other, here’s some fun and sweet things you can do at Potawatomi Hotel & Casino and around the city.

Sweetest Day Date Ideas at Potawatomi Hotel & Casino


1)    Live Music: If live music is the way to your sweetheart’s heart, the Northern Lights Theater has a variety of terrific shows going on this month, with acts like Sheena Easton, Clint Black, Mark Farner’s American Band and Ruben Studdard, delighting audiences with the gift of song and dance no matter what genre you love.

2)    Live Comedy: Bring your date to a Bonkerz! Comedy Club show to make them laugh! This month we have comedic acts Adam Ferrara and Mike Terryfield on Saturday, October 26 at 7:00 p.m. and 9 p.m. Sit back and have a good laugh with your sweetheart. We’re sure you’ll leave feeling refreshed and energized to continue a night of more laughs and fun.

3)    Share Your Heart: Sweetest Day actually started out as a charitable holiday. A committee of confectioners distributed free candy to “newsboys, orphans, old folks, and the poor.” If you’d rather take this approach while also having a bit of fun, consider playing Canal Street Bingo. Proceeds will go to children’s charities throughout the Milwaukee area.

4)    Bet on Love: If you’ve walked our casino floor before then you know that we have quite a few machines dedicated to love. If your sweetheart loves to play games, then download our app to find Hearts of Fire, Love and War, Heart Throb, I Heart Jackpots, and our sweetest machine: Reel Sweet Stacks.

No matter what kind of entertainment you’re into, Potawatomi Hotel & Casino has plenty of options to spend a magical night enjoying your significant other’s company.

Romantic Meals

5)    Champagne Breakfast: While our Buffet is well known for it’s champagne breakfast, that only happens on Sundays. You can treat your partner to a delicious breakfast and champagne everyday at Canal Street Café. They serve breakfast all day every day, so whether you’re going in for breakfast, lunch, dinner or anywhere in between, you can rest knowing you will get what you’re craving. Look out for our weekly specials and other yummy comfort classics that our Canal Street Café team creates.

6)    Fine Dining: Enjoy fine dining in a relaxed atmosphere when you bring your sweetheart to Dream Dance Steakhouse. Our new and improved fall menu has a wide selection of wines (we’re talking hundreds) for every type of palate out there. Share your favorite bottle of wine over a delicious steakhouse dinner and dessert. Don’t have a favorite bottle or label? We’ll help you find it.

7)    Italian Dinner: If pasta is more fitting to your taste, Bella Italiana has fresh-made pasta and mouthwatering Italian entrée favorites like chicken marsala, Sicilian steak or Delmonico steak. Order some tasty sides and share them with each other because what’s good food for if not meant to share. You have room for dessert? Try the tiramisu, the limoncello cheesecake or the double chocolate cake to share.

8)    Sweet Indulgence: Now what is Sweetest Day without actual sweets? The Buffet has a variety of sweet and tasty dessert options to satisfy anybody’s sweet tooth, including chocolate cupcakes, apple Bettys and chocolate. Make your selection of delectable treats to share with your sweetheart, prepared by our in-house pastry department. Did you know all of our restaurants’ scrumptious desserts are created for our guests by the talented hands our pastry team? So all your favorite cheesecakes, cookies, cakes and everything in between are always made fresh and flavorful.

9)    Happy Hour: Enjoy a drink or two at one of our bars while you enjoy each other’s company. Don’t miss any of this month’s drink specials including $3/$6 Bacardi® mixers and $3 bottles of Modelo Especial®, a full-flavored Mexican lager.

With so many delicious and prize-winning restaurants on property, we make it easy to surprise your significant other with three magic words that will make them melt with excitement: “I made reservations.”

Rest & Relaxation

10)    Couple’s Massage: Maybe you or your love have been working hard and need to destress? Why not come in for a couple’s massage at Ember Spa so you can unwind together. With a variety of oils and scents, you can make yours as special as you want it to be.

11)    Spa Day: The new year is right around the corner and with it comes an opportunity to reinvent yourself. If the fall season is the perfect time for you to get a new look, why not surprise each other with a new cut, color or manicure (or all three)? Leave feeling brand new once our spa team is done doing their magic and then plan a night on the town to debut your new looks, feeling fresh and chic.

12)    Staycation or Vacation: Stay the night at one of our newest hotel rooms and indulge yourself with the views of the Milwaukee skyline in the background. Now who wouldn’t want to enjoy a beautiful sunset with your loved one by your side? Whether it’s spending a night on the town or enjoying the weekend to yourself with your own special mini staycation, our hotel is only a short drive away from all the fun things happening in the Milwaukee nightlife.

Make sure you celebrate your loved one and express your love however you prefer this Sweetest Day weekend. Who knows? Your next visit here might include a sweet honeymoon.

Looking for other romantic date ideas in Milwaukee? Here’s a handy checklist of things if you need help thinking of ways to surprise your loved one for this Sweetest Day.

28 More Milwaukee Date Ideas for Sweetest Day

1.     Take a walk along the lakefront or the Riverwalk and enjoy a nice conversation together

2.     Ride The Hop ride together downtown with stops at your favorite shops and restaurants

3.     Write them a letter with all the things you love about them and read it out aloud

4.     Switch up your date night and go to any of Milwaukee’s adult arcades like UpDownMKE, Nine Below or our very own Topgolf® Swing Suite bays

5.     Spend the day together at the Milwaukee Public Museum; learn about Potawatomi culture and history at the permanent exhibition A Tribute to Survival

6.     See beautiful art pieces at the Milwaukee Art Museum and purchase beautiful art pieces like jewelry or souvenirs for your home as a sweetest day gift

7.     Try a restaurant you’ve never gone to before. It’s Milwaukee, there’s always something popping up and delicious food is never a problem in this city. 

8.     Spend a night in and cook your favorite dishes together for each other.

9.     Don’t miss fun Halloween celebrations at the Milwaukee County Zoo this month, including Boo at the Zoo on October 18 & 19 and the Halloween Spooktacular on October 25 & 26.

10.  Take a horse-drawn carriage ride around downtown: https://mkecarriage.com/special-events/

11.  Plan an intimate picnic or go fishing together at Lakeshore State Park

12.  Grab delicious rooftop drinks by the fire at The Outsider

13.  Kayak down the Milwaukee River together and enjoy the beautiful sights and sounds along the way

14.  Climb to the top of the North Point Lighthouse (Don’t miss the beautiful photo op!)

15.  Indulge in a Milwaukee classic like custard at Kopp’s or Leon’s for a late-night treat

16.  Experience a romantic dinner at the Edelweiss Oktober Dinner cruise.

17.   Share small bites at Movida or try a varied selection of street food from all around at Zocalo Food Truck Park. There’s plenty of drink options to choose from too.

18.  Enjoy apple-picking and pumpkin-picking season and after you’ve finished making your selection, check out the variety of delicious fresh food available at each farm.

19.  Try your hand at Koz’s Mini Bowling! Bring some friends, the more, the merrier!

20.  Drinks at Bryant’s Cocktail Lounge

21.  Watch a movie at the Rosebud in Wauwatosa and/or the Oriental on the East Side.

22.  Plan your next date night and don’t miss this month’s Milwaukee Film Festival from October 17-31 or any of the films as part the Native American Heritage Month film series next month!

23.  Stop by our Bingo Hall on the last Saturday of the month for GLOW BINGO for a date night.

24.  Enjoy a great beer selection at the Sugarmaple. Beforehand, grab dinner at any of Bayview’s adorable joints including; Café LuLu, Honeypie, Odd Duck, Café Corazon or Hungry Sumo.

25.  For all those couples that just love to dance, get down and jive at Daync Studio on Hamilton St. on Friday nights or Freight 38 on Saturday nights.

26.  Milwaukee has plenty of terrific beer to offer, so why not give it a try by visiting any of your favorite breweries? Try Third Space Brewing Company or City Lights Brewing Company right here in the Menomonee Valley.

27.  Go to any of this season’s Bucks game and celebrate basketball season Milwaukee style at the Fiserv Forum.

28.  Chase the thrill and excitement together at the Fear District, with scary houses, monsters and ghouls. (Cozy cuddles are not required, but encouraged)